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Discover Tuscany’s charm on this private tour featuring San Gimignano, two local wineries, wine tastings, and a light lunch—perfect for wine lovers and culture seekers.
Exploring Tuscany’s Hidden Gems: A Deep Dive into the Chianti, SuperTuscan & San Gimignano Tour
This private tour from Montecatini Terme offers a taste of Tuscany’s best, combining the medieval charm of San Gimignano with visits to two boutique wineries. For those looking to enjoy authentic wine and stunning scenery in a relaxed, personal setting, this experience might just be the highlight of your trip.
What makes this tour particularly appealing? We love the intimacy of the private format, allowing for more personalized interactions with local wine producers and guides. The opportunity to explore San Gimignano’s iconic towers, combined with wine tastings that include insights into production and tasting techniques, adds a valuable layer of understanding.
However, one potential consideration is the cost—at $459.81 per person, it’s an investment, but considering the inclusions and the personalized experience, the value can be quite high for lovers of good wine and authentic regions.
This tour is best suited for travelers who want a deeper, more personalized glimpse into Tuscany’s wine culture, enjoy scenic village visits, and appreciate quality experiences over crowds and commercialized tours.

Looking for more options in Montecatini Terme? Here are some other experiences worth considering.
Starting from Montecatini Terme, this tour offers the kind of flexibility and personal attention that larger group excursions rarely deliver. With only your group participating, guides like Massimo or Vito focus entirely on your interests, sharing local stories, wine tips, and cultural insights that bring Tuscany alive. The transportation is arranged for convenience, with pickup and drop-off included, so you can relax and soak in the scenery without worrying about navigation or schedules.
The first stop is the enchanting town of San Gimignano, a UNESCO World Heritage site famous for its skyline of medieval towers. This town, with its narrow streets and centuries-old architecture, exudes a timeless charm. Visitors often comment on how beautiful and well-preserved the town is, making it a perfect spot for a gentle walk, photos, and soaking in the local atmosphere.
While 50 minutes might seem brief, it’s enough to enjoy the main sights and get a feel for the town’s unique character. Some reviews highlight the value of this time: “The town of San Gimignano was beautiful and a perfect introduction to Tuscany,” as one guest noted.
Following San Gimignano, the tour takes you to two carefully selected local wineries. Instead of large commercial operations, these are boutique wineries where the hosts are genuinely passionate about their craft. Guests like Jule_H mention feeling like visiting “old friends,” thanks to the personal approach of the hosts.
You’ll walk through cellars where wine is aged in barrels, learning about the process from grape to glass. The guides make a point of explaining how different types of wine, especially the renowned SuperTuscan, are crafted. Expect to taste a variety of wines, including Chianti and SuperTuscan blends, and perhaps sample some local snacks.
One of the highlights is learning how to taste wine like a pro. Guides provide insights into aroma, palate, and the visual cues that identify quality. Reviewers, like Denise_D, appreciated how friendly and knowledgeable the staff were, making the tasting both educational and enjoyable.
An authentic experience like this isn’t just about drinking but gaining a deeper appreciation for Tuscany’s wine culture. This is especially true with the insights shared by hosts, who often go beyond tasting to tell stories about their families and traditions.
While the tour includes wine tasting, a light lunch is available for 75 Euro per person (children 35 Euro). Though it’s not included in the base price, this meal often receives praise for its quality and filling nature. Guests mention that Jessica and her family serve up delicious local fare, making the lunch a memorable highlight.
The views from the wineries are almost as spectacular as the wines themselves, with vineyards stretching into the horizon—perfect for a relaxed meal and more conversation about Tuscany’s culinary delights.
Multiple guests emphasize how special this tour is. One mentioned their guide, Simona, made the experience feel like visiting old friends, highlighting the importance of personal connection. Another described Massimo as “truly amazing,” noting his kindness and knowledge, which made the day even more memorable.
Guests also appreciated the balance of scenery, culture, and wine. The feeling of being welcomed into small, family-run wineries creates an authentic vibe not often found in larger tours. The time spent in San Gimignano, combined with the wine and food, offers a well-rounded immersion in Tuscany’s charm.
At $459.81, the tour is an investment in a premium experience. However, considering the inclusion of private transport, guided visits, two winery tours, tastings, and the scenic village stop, many find the value justified. The tour typically books about 75 days in advance, so planning ahead is advised.
It lasts about 7 hours, allowing you to enjoy a relaxed pace without feeling rushed. The small-group nature ensures a more intimate experience, which is especially appealing if you value genuine interactions.
The tour is suitable for most travelers, with clear guidelines about children under 18 not drinking wine and the need for specific dietary restrictions to be communicated in advance. The booking is flexible with free cancellation up to 24 hours prior, giving you peace of mind.

This experience is a fantastic pick for wine aficionados, history buffs, and culinary travelers alike. If you’re seeking a personalized, authentic way to explore Tuscany beyond the crowded tourist spots, this tour delivers. It’s particularly perfect for those who enjoy learning about wine production, savoring regional flavors, and soaking in breathtaking views.
Travelers who appreciate small-group intimacy and local hospitality will find this tour especially rewarding. It’s an excellent way to connect with Tuscan culture through its wine, food, and historical charm—all in one memorable day.
While it’s on the higher end price-wise, the quality of the experience, the insightful guides, and genuine visits to family-run wineries make it stand out as a worthwhile investment for a truly authentic Tuscany adventure.
Is this tour suitable for children?
Yes, children can participate but are not allowed to drink wine. The experience is family-friendly, with the tour guiding and visits designed for all ages, but kids need to be accompanied by an adult.
How many wineries will I visit?
You will visit two wineries, where hosts will share their craft and stories. The visits are carefully selected for authenticity and quality.
What’s included in the tour price?
The base price covers transportation, a driver/guide, visit to San Gimignano, and private winery visits. Wine tastings are included in the tour price, but the light lunch is optional and paid separately.
Can I cancel if my plans change?
Yes, with free cancellation available up to 24 hours before the tour. After that, cancellations are non-refundable.
How long does the tour last?
The tour lasts approximately 7 hours, offering ample time for sightseeing, wine tasting, and enjoying the scenery without feeling hurried.
What should I wear or bring?
Comfortable shoes for walking, sun protection, and a camera are recommended. If you have specific food restrictions, be sure to inform the provider in advance.
Is the tour accessible for people with mobility issues?
Most travelers can participate, but due to walking in towns and wineries, it’s best to check specific mobility needs with the tour provider beforehand.
Are there any hidden costs?
The tour price covers most major aspects. Additional costs might include the optional light lunch (75 Euro per person) and any extra purchases at wineries.
How far in advance should I book?
Given the typical booking window of about 75 days, it’s advisable to reserve at least a couple of months ahead to secure your preferred date.
To sum it up, this private Chianti, SuperTuscan & San Gimignano tour packs a lot into one day. It’s ideal for those who want a personalized, insider’s look at Tuscany’s wine and historic town life, all while enjoying stunning views and delicious regional flavors. While the price is on the higher side, the quality, intimacy, and authentic encounters make it a worthwhile splurge for anyone eager to truly understand and taste Tuscany. Whether you’re a dedicated wine lover or someone craving an authentic cultural experience, this tour promises a memorable day of discovery and delight.